The synthesis of functionalized oxindoles and benzofuranones via oxidation of 2-BMIDA indoles and benzofurans, respectively, is described. Interconversion of boron species (BMIDAàBF3K) was necessary to enable oxidation and overcome boronic acid stability issues associated with a difficult BMIDA hydrolysis. Overall, a robust process was developed that allowed access to a small library of oxindole and benzofuranone products and facilitated the step-efficient synthesis of biologically-active compounds containing the oxindole pharmacophore.
- functionalized oxindoles synthesis
- boronic acid stability
- oxindole pharmacophore
Seath, C. P., Fyfe, J. W. B., Molloy, J. J., & Watson, A. J. B. (2016). Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs. Synthesis. https://doi.org/10.1055/s-0035-1562619